Q01
Question — Tell me about the last new software, data, hardware, or outside-service purchase the firm approved. Who requested it, who owned the budget, who signed, and who could have blocked it?
Uncovers — Decision chain, budget authority, veto points, internal sponsorship.
Why it stays clean — It anchors authority in a real approved purchase.
Follow-up probes —
- What was the approval threshold?
- Which department’s budget did it hit?
- Who was consulted but did not sign?
Polite-answer trap — Useless/evasive: “It goes through management.” Redirect: “For the last approved purchase, whose name was on the request and whose name was on the approval?”
Q02
Question — What are the spending thresholds where a project manager, department head, director, finance, IT, or the board becomes involved?
Uncovers — Price bands, approval friction, budget ceiling, buyer escalation.
Why it stays clean — It asks for existing rules and thresholds, not acceptable prices.
Follow-up probes —
- What can be approved on a company card or purchase order?
- What requires multiple quotes?
- What amount triggers board or group review?
Polite-answer trap — Useless/evasive: “It depends on the circumstances.” Redirect: “Could we use the last three purchases as examples and note who had to approve each?”
Q03
Question — When a genuinely unfamiliar tool or vendor appears, what checks happen before the first payment is made?
Uncovers — Procurement burden, security review, vendor onboarding, data restrictions.
Why it stays clean — It asks about real process applied to unfamiliar vendors.
Follow-up probes —
- Who performs the checks?
- Which document or questionnaire is required?
- What was the last vendor delayed by these checks?
Polite-answer trap — Useless/evasive: “We do the normal due diligence.” Redirect: “What did the normal due diligence require on the most recent unfamiliar vendor?”
Q04
Question — What was the last purchase that IT, security, finance, legal, insurance, or a client slowed down or stopped?
Uncovers — Institutional blockers, compliance friction, procurement risk.
Why it stays clean — It asks for an observed blocked or slowed purchase.
Follow-up probes —
- Which function raised the issue?
- What exact concern was raised?
- Was the purchase changed, delayed, or abandoned?
Polite-answer trap — Useless/evasive: “There are checks, but nothing unusual.” Redirect: “Which purchase took longer than expected because of one of those checks?”
Q05
Question — How does project-level budget differ from head-office or group budget when buying tools or outside help?
Uncovers — Budget ownership, project chargeability, central-local tension.
Why it stays clean — It asks how previous spending was classified and approved.
Follow-up probes —
- Which costs can be charged to a project?
- Which must sit in overhead?
- Which route is easier politically?
Polite-answer trap — Useless/evasive: “It can be either.” Redirect: “For the last purchase, where did the cost actually land?”
Q06
Question — Who has authority to start a small paid trial, and what must happen before that trial becomes a wider purchase?
Uncovers — Trial authority, conversion hurdles, expansion process, buying stages.
Why it stays clean — It asks about existing authority and past conversion rules, not trial interest.
Follow-up probes —
- What was the last small trial someone approved?
- What evidence was required before expansion?
- Who said yes or no at the next stage?
Polite-answer trap — Useless/evasive: “We can trial things if they make sense.” Redirect: “Which trial was actually paid for most recently, and who approved it?”
Q07
Question — How are renewals reviewed differently from new purchases?
Uncovers — Incumbent advantage, budget inertia, cancellation friction, renewal standards.
Why it stays clean — It asks for existing renewal behavior rather than buying intent.
Follow-up probes —
- Who owns the renewal calendar?
- What usage or value evidence is requested?
- Which renewal was escalated most recently?
Polite-answer trap — Useless/evasive: “Renewals are handled case by case.” Redirect: “What happened on the last renewal that was not simply rubber-stamped?”
Q08
Question — Which purchase required a data-processing agreement, security questionnaire, client permission, or contractual review?
Uncovers — Data sensitivity, compliance burden, legal friction, risk tolerance.
Why it stays clean — It asks for completed paperwork and approvals from a real purchase.
Follow-up probes —
- What data was involved?
- Who completed the paperwork?
- How long did that step take?
Polite-answer trap — Useless/evasive: “We are careful with data.” Redirect: “Which named vendor or tool last triggered a data or security review?”
Q09
Question — What was the fastest purchase the firm made in the last year, and what made the normal process faster?
Uncovers — Urgency, bypass routes, sponsor power, exceptional circumstances.
Why it stays clean — It asks for a real exception that reveals true authority.
Follow-up probes —
- Who accelerated it?
- What threshold or policy was bypassed or compressed?
- What problem made speed acceptable?
Polite-answer trap — Useless/evasive: “We move quickly when needed.” Redirect: “Which purchase moved fastest from first discussion to payment?”
Q10
Question — What was the slowest purchase or approval in the last year, and where did the time go?
Uncovers — Procurement latency, bottlenecks, veto power, implementation delay.
Why it stays clean — It asks for a concrete delayed purchase instead of generic procurement pain.
Follow-up probes —
- How many weeks or months passed?
- Which step consumed the most time?
- Who had to chase it?
Polite-answer trap — Useless/evasive: “Procurement can take time.” Redirect: “Which named purchase took the longest, and what were the dates from first request to approval?”